Question 16.53: Write the structure of the amino alcohol formed in the react......

Organic Chemistry Study Guide: Key Concepts, Problems, and Solutions [1424398]

Write the structure of the amino alcohol formed in the reaction of (2S,3R)-2,3-dimethyloxirane with aqueous ammonia. Explain why this compound forms in preference to a diol. Assign the stereochemistry of each chiral center in the product.

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Ammonia is a better nucleophile than water. The reaction occurs with inversion of configuration at the center attacked by the nucleophilic ammonia. Attack at one carbon atom gives the (2R,3R) product, and attack at the other carbon atom gives the (2S,3S) product. Thus, a racemic mixture of enantiomers results.

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